(1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol

Base Information

• Chemical Name: (1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol
• CAS No.: 215026-24-7
• Molecular Formula: C₂₀H₂₀O₃
• Molecular Weight: 308.377
• Mol file: 215026-24-7.mol

Synonyms:(1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol

Chemical Property of (1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol

There total 12 articles about (1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

(2S,3S,4aR,5R,6R,8aS)-2,3-Diphenyl-6-phenylselanyl-octahydro-benzo[1,4]dioxin-5-ol → (1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol (215026-24-7)

Guidance literature:

With dihydrogen peroxide; In tetrahydrofuran; ethanol; Heating;

DOI:10.1016/j.tet.2005.01.003

Reference yield:

(1S,3S,4S,6S,7S,8S)-3,4-diphenyl-2,5-dioxa-7,8-epoxybicyclo[4,4,0]decane (215026-22-5) → (1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol (215026-24-7)

Guidance literature:

Multi-step reaction with 2 steps

1: NaBH₄ / ethanol / 4 h / Heating

2: 97 mg / H₂O₂ / ethanol; tetrahydrofuran / Heating

With sodium tetrahydroborate; dihydrogen peroxide; In tetrahydrofuran; ethanol;

DOI:10.1016/j.tet.2005.01.003

Reference yield:

(S,S)-hydrobenzoin (2325-10-2) → (1S,3S,4S,6R,7S)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol (215026-24-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 55 percent / NaH / dimethylformamide; various solvent(s) / 1 h / 20 °C

2: 33 percent / AgOTf / CH₂Cl₂ / 0.5 h / -78 °C

3: 90 percent / NaIO₄; NaHCO₃ / methanol; H₂O / 48 h / 90 °C

4: 89 percent / dimethyldioxirane / acetone / 3 h / 0 °C

5: NaBH₄ / ethanol / 4 h / Heating

6: 97 mg / H₂O₂ / ethanol; tetrahydrofuran / Heating

With sodium tetrahydroborate; sodium periodate; dihydrogen peroxide; silver trifluoromethanesulfonate; 3,3-dimethyldioxirane; sodium hydride; sodium hydrogencarbonate; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.tet.2005.01.003

upstream raw materials:

(S,S)-hydrobenzoin

rac-3-bromocyclohexene

(1S,3S,4S,6R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-7-ene

(1S,3S,4S,6S,7S)-3,4-diphenyl-7-phenylseleno-2,5-dioxabicyclo[4,4,0]decane

Downstream raw materials:

(1S,3S,4S,6R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-one

(1S,3S,4S,6R,7R)-3,4-diphenyl-2,5-dioxabicyclo[4,4,0]dec-8-en-7-ol

7,8-diphenyl-3a,5a,7,8,9a,9b-hexahydro-1,3,6,9-tetraoxa-cyclopenta[a]naphthalen-2-one

2,3-diphenyl-octahydro-benzo[1,4]dioxine-5,6,7,8-tetrol